Ici 109,081 → HCID 13193385, compound

HRID 463657Notes

Reaction equation

HRID 463657 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[C:16]([C:18]([CH3:23])([CH3:22])[C:19](Cl)=[O:20])#[N:17]>N1C=CC=CC=1>[C:16]([C:18]([CH3:23])([CH3:22])[C:19]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)=[O:20])#[N:17]

Participants

4

Reactant 2

HCID 161928Ici 109,081HCID 202649072-Cyano-2-methylpropanoyl chloride

Product 1

HCID 13193385HCID 13193385, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

20.3 g (0.1 mole) of 6-(p-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone were stirred with 15.8 g (0.12 mole) of 2-cyano-2-methylpropionyl chloride in 100 ml of pyridine for 3 hours at 0° C. 100 g of ice were added, after which the crystals were filtered off under suction, and the product was recrystallized from dimethylformamide/water and dried at 50° C. under greatly reduced pressure. 20.5 g (57%) of 6-[p-(2-cyano-2-methylpropionylamino)-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone were obtained. Mp.: 225°-227° C.

Workup

  1. filtrationafter which the crystals were filtered off under suction
  2. customthe product was recrystallized from dimethylformamide/water
  3. customdried at 50° C. under greatly reduced pressure

Sources & evidence

ORD record
ord-964ecc6452a244308ff1c25a998f7e7e
Source dataset
uspto-grants-1985_10
Patent number
US04544562

Reaction notes

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